The IT Cert Roadmap for 2026: Which Certs, in What Order, and What to Skip

There are hundreds of IT certifications, and most career advice either lists all of them or pushes whatever a course sells. This is the order I’d follow if I were starting from zero today, based on the route I took from a repair bench to senior systems administrator at a managed service provider.

Short on time? The free two-page roadmap PDF has the whole thing on one sheet.

The short version

1. Get hired: CompTIA A+, Network+, Security+
2. Move up: Microsoft AB-650 and MD-102
3. Cloud: Microsoft AZ-900 (optional), then AZ-104
4. Specialize: Cisco CCNA for networking, or CompTIA CySA+ for security

One cert at a time, in that order. Each one builds on the last, and each phase lines up with a real job title you can apply for.

Phase 1: Get hired

CompTIA A+ (two exams, roughly $265 each). Hardware, operating systems, and troubleshooting. It’s the filter most help desk postings use.

CompTIA Network+ (roughly $390). IP addressing, DNS, DHCP, VLANs, and routing. Every ticket eventually touches the network, and this is where you learn why.

CompTIA Security+ (roughly $425). Security fundamentals, and the cert many government and defense contractor IT jobs require. If you’re a veteran, this one opens a lot of doors.

Target jobs: help desk, desktop support, MSP technician. Don’t wait until all three are done to apply. Once you have A+ and you’re studying for Network+, start applying.

Phase 2: Move up with Microsoft

At an MSP, almost every client runs Microsoft 365, Entra ID, and Intune. These two certs line up with the work you’ll actually be doing once you’re off the help desk.

Microsoft AB-650: Administering Microsoft 365 and AI Services ($165). Running a Microsoft 365 tenant: users, identity, Defender, Purview, and Copilot. This replaces MS-102, which Microsoft retires on November 30, 2026. Don’t start studying for MS-102 now.

Microsoft MD-102: Endpoint Administrator ($165). Managing laptops and phones with Intune and Autopilot. Microsoft updated the exam objectives on October 27, 2026, so make sure your study material covers the new version.

Target jobs: systems administrator, Microsoft 365 administrator, MSP tier 2.

Phase 3: Cloud

Microsoft AZ-900: Azure Fundamentals ($99). Cloud concepts and core Azure services. It’s optional. If your Microsoft 365 work already has you in Azure, you can go straight to AZ-104.

Microsoft AZ-104: Azure Administrator ($165). Identity, virtual machines, networking, and storage in Azure. This is the cert cloud job postings ask for by name, and it’s the one I’m working on now.

Target jobs: cloud administrator, Azure engineer.

Phase 4: Specialize

By now you’ll know which part of the work you like. Pick one:

• Cisco CCNA (roughly $300) if you like networking: routing, switching, and the deep troubleshooting network engineers get hired for.
• CompTIA CySA+ (roughly $425) if you like security: threat detection, log analysis, and incident response for SOC and blue team roles.

What to skip

• Retired Microsoft exams. MS-900 retired March 31, 2026, AI-900 retired June 30, 2026, and MS-102 goes on November 30, 2026. Check Microsoft’s retirement list before you buy any course.
• The coding detour, if you’re aiming for infrastructure. I spent real time on a web development course early on, and it didn’t lead anywhere for the work I ended up doing. Put that time into the cert path and a home lab.

Study for free

• Professor Messer for CompTIA videos and notes.
• Microsoft Learn for every Microsoft exam, including free practice assessments.
• Cisco Packet Tracer for CCNA labs.
• A home lab for everything. Reading gets you through the exam. A lab gets you through the interview.

Keeping them current

CompTIA certifications are good for three years, and you renew them with continuing education. Microsoft associate certifications expire every year, but renewal is a free online assessment on Microsoft Learn.

Veterans: don’t pay out of pocket first

• COOL (cool.osd.mil): each branch’s credentialing program funds cert exams for eligible service members.
• GI Bill test reimbursement: VA pays back approved certification test fees up to $2,000 per test, pass or fail.
• VET TEC 2.0: covers eligible tech training programs for veterans. It doesn’t cover exam fees.
• DoD SkillBridge: a civilian internship in your last 180 days of service, still on military pay.

Program rules change, so confirm with the VA or your branch before you count on the money.

Get the roadmap

Prices above are approximate US exam costs as of October 2026. For the whole route on two printable pages, including the home lab builds and resume tips, download the free IT career roadmap. Questions? Ask here.